


Loop of Despair

by LadyArtemisia28



Category: Supernatural
Genre: Alcohol Abuse/Alcoholism, Angst with a Happy Ending, Blood, Castiel Loves Dean Winchester, Dean Winchester Loves Castiel, Dean Winchester is Bad at Feelings, Episode: s15e18 Despair - Castiel's Confession Scene, Fix-It, God | Chuck Shurley Being an Asshole, Homophobic Language, Implied/Referenced Homophobia, M/M, Major Character Injury, Sad with a Happy Ending, Self-Harm, Suicidal Dean Winchester, The Empty (Supernatural), Time Loop
Language: English
Status: In-Progress
Published: 2021-01-12
Updated: 2021-02-02
Packaged: 2021-03-16 09:27:35
Rating: Mature
Warnings: Major Character Death
Chapters: 4
Words: 7,379
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28704411
Author URL: https://archiveofourown.org/users/LadyArtemisia28/pseuds/LadyArtemisia28
Summary: Dean Winchester could not believe that his best friend, Castiel was confessing his feelings of love towards him.But the message does settle in by the 4th or so time that he hears it.15x18 time loop.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Comments: 12
Kudos: 71





	1. It Hurts like Hell

**Author's Note:**

> Chapter Title in reference to the Song 'Hurts like Hell' By Fleurie

**Summary for the Chapter:**

> Loops 1-4

~

Dean momentarily blacked out as his heart began to physically fail him. He found himself coming back to consciousnesses standing hunched over near the entrance to the room. Dean sighed in relief as he looked over to see Castiel finishing up painting a protective sigil on the door with his angelic blood.

Dean could feel the literal death grip on his heart ease.

“Did it work?” Castiel asks and receives a nod as an answer. “I blocked her grip on you”

Knock

“Dean she said that wound was killing her.” Cas should with a small bit of hope in his voice. A knock interrupts his words. “Maybe we can wait her out.”

Dean walks away from Cas “Yeah and if we can't?”

“Then we fight” he replies as he looks back at the door which has another knock coming from it.

“We'll lose” Dean says as he reaches the chair in the middle of the demon circle. He turns to look at Cas who is now looking back as he continues his negative spiral. “I just led us into another trap.”

Another knock

“All because I couldn't hurt Chuck” he looks downward. Another knock. “Because I was angry and because I just needed something to kill and because that is all I know how to do.”

“Dean” Cas says resolute as he approaches him

“It was Chuck all along.”  
Knock

“We never should have left Sam and Jack we should be there with them now”  
knock

“Everybody's gonna die, Cas. Everybody. I can't stop it”  
knock

This time they both look at this knock while Dean moved towards Cas

“She's gonna get through that door ”

Cas looks away from Dean while he replies “I know”

“And she's gonna kill you. And then she's gonna kill me”  
Cas glances briefly at Dean and then looks away once again.

Dean sighs and looks down before he says “I'm sorry”

Cas looks into the middle distance back and forth like he was going over a plan in his mind. He appears to have found something, gulps and furrows his brow with determination

“Wait there is.”

Dean raises his head and turns his face to look at Cas with the smallest glimmer of hope.

“There's one thing she's afraid of. There's one thing strong enough to stop her.” He finally turns his face to look at the eldest Winchester.

Dean looks at Cas and gulps listening intensely as Cas looks away.

“When Jack was dying, I...I made a deal” Cas returning his eyes to look at him once more. “To save him.”

“You what?” 

“The... the price was my life” Cas says his eyes beginning to water with feeling “When I experienced a moment of true happiness The Empty would be summoned and it would take me forever”

Dean's face was confused as he struggled with a responses.

“Why are you telling me this now?”  
knock

“I always wondered” Cas's face turned to look away for the briefest of moments before he quickly found the resolve to turn his gaze fully at Dean. “Ever since I took that burden, that curse, I wondered what it could be. What my true happiness could even look like?”

“And I never found a answer”

“Because the one thing I want is something I know I can't have.”

Knock

Dean is confused and silent.

“But I think I know, I think I know now. Happiness isn't in the having...it's in just being it's in just saying it.”

Dean has to break his silence and ask in confusion.

“What are you talking about Man?”

Cas has a brighter expression on his face as he takes a step forward towards Dean.

“I know, I know how you see yourself Dean. You see yourself the same way our enemies see you. You're destructive, you're angry, You're Broken. You're Daddy's blunt instrument.”

“You think that hate and anger that's what drives you, that's who you are.”

“It's not. And everyone who know so you sees it. Everything you have done the good and the bad you have done for Love.”

“You raise your little brother for love, You fought for this whole world for love. That is who you are.”

Dean can no longer hold his gaze. 

“You're the most caring man on earth. You are the most selfless loving human being I will ever know.”  
Cas's sad smile 

The knocking sounds further away at the moment.

“You know ever since we met, ever since I pulled you out of hell” a tear rolls slowly down Cas's right eye “Knowing you has changed me. Because you cared I cared. I cared about you, I cared about Sam, I cared about Jack, I cared about the whole world because of you”

“You changed me Dean”

“Why does this sound like a goodbye?” Dean asks still very confused at what was happening.

“Because it is”

“I love you”

“Don't do this Cas” Dean pleads for him to not be saying these words as a goodbye.

One final knock.

The Empty appears behind Dean and he turns to look. Then quickly back at Cas as the door slams open Billie appearing behind it.

“Cas” Dean starts to say. Too many things are happening at once, he feels overwhelmed.

Cas places his blood covered right hand on to Dean's left shoulder

“Goodbye Dean”

He shoves Dean to the floor before Dean can protest. Cas gives him one final fond look and then takes a breath.

The Empty grabs both of the otherworldly beings.  
Dean is left with the silence before all of the emotion and tears break free.

~

Dean momentarily blacked out as his heart began to physically fail him. He found himself coming back to consciousnesses standing hunched over near the entrance to the room. Dean blinked in confusion as he looked over to see Castiel finishing up painting a protective sigil on the door with his angelic blood.

Dean could feel the literal death grip on his heart ease.

“Did it work?” Cas asks with concern.

“Wha...what's happening?” Dean asks as he shakes his head to try and clear the fog

“Billie is coming after us.”

Dean stayed silence as Cas continued speaking. His words began to give Dean a sense of déjà vu 

“Wait...this” he says quietly to himself.

He stares at Cas who continues telling him about his deal and telling Dean about how he was not a killer and how he was motivated by love.

Once Dean hears the words “I love you” he turns to look behind him a split second faster than he did originally. 

He sees the empty and just panics.

“Take me you fucking tar pit!” Dean shouts as he runs full speed at it ignoring the panicked shout of his name behind him.

The inky darkness stilled as he threw himself at it.

~

He found himself coming back to consciousnesses standing hunched over near the entrance to the room. Dean blinked with shock as he looked over to see Castiel finishing up painting a protective sigil on the door with his angelic blood.”

“Did it....”

“Cas, we are in a time loop” Dean interupts

“What?”

“You summon the empty and you...”

“I summon the empty? But how?” 

Dean could scream, _'You fucking idjit! You gave him the idea!'_

“You say a whole bunch of shit about me. I think letting me think that you love...”

“What?”

“Which is such a dick move. The way you say it is really...”

“Dean”

“The one thing you can't have? Like what do you think I'm going to think when you say that?!”

“DEAN!”

“WHAT?!”

“I DO LOVE YOU!”

...  
.....

“...what?” 

He places his hand back on the same shoulder

“I love you,”

“Uh, like a brother right?” Dean asks with an eyebrow raise. He momentarily forgets about the time loop. Cas gives him a look of amusement. 

Dean trys to make sense of what Castiel is saying to him. 

“You love me? As in flowers, and chocolates,....uh” Dean gulps before weakly asking “kissing?”

“I'm sorry if this has made you um, uncomfortable. But just saying my truth is what was needed to make me happy. I feel an incredible amount of peace now. I am sorry I was not brave enough to tell you at an earlier time."

This caused Dean to remember what was coming. Or in this cause, what had already arrived. In his pure confused and shocked state he had completely ignored that The Empty had already made it's arrival. 

“NO!” Dean shouted as he turned to look back and feel the hand hit his shoulder as he heard Cas's final words to him again. 

“Goodbye Dean.” 

He was again at the moment where he was pushed away to the ground. This time he happened to find his voice..

“Cas, stop!" He yelled helplessly. 

After the disappearance of Castiel happened again Dean just wordlessly screamed at full volume.

~

Dean momentarily blacked out as his heart began to physically fail him. He found himself coming back to consciousnesses standing hunched over near the entrance to the room. Dean blinked this time with anger as he looked over to see Castiel finishing up painting a protective sigil on the door with his angelic blood.

Dean could feel the literal death grip on his heart ease.

“Did it work?” 

Dean ignores Cas's question as he steadys his body and then rushes over to the storage boxes.

_'Okay so telling him did NOT work, Damnit! I see now why Sammy was so pissed off during his Groundhog day loop.'_

“We have to find SOMETHING in this room to help us with this!” Dean shouts He makes an angry noise at knock behind him. 

“Why do we have all this useless shit!” 

“What the fuck is this?!” Dean asks as he holds up spiky crown.

“That is uh the crown of thorns” Cas replies. “That would be of no use to us in this situation.”

“If it can't stop Billie then WHAT USE IS IT!!!” Dean yells as he throws it full force at the wall.

“There is one thing that is strong enough” 

Dean's head shot up his eyes wide to look at Cas's face.

“NO no nonono!” he moves back towards him.

“Don't you dare Cas.” he growled at him with a pointed finger.

“Dean, I have something you need to hear.”

“I will set your fine feathery ass on fire with holy oil if you keep on speaking your truth or whatever.”

He brushed past his accidentally blurted out flirty comment.

Cas tries to start his speech when Dean decks him.

It only gives him brief pause. 

All it does is cause him to head tilt and stare at Dean with confused narrowed eyes.

“what, was that Dean?”

“See I AM fueled by ANGER! You can't tell me otherwise!” Dean laughs mirthlessly. “Don't lie to me!”

“No you are caring you are fueled by love.”

“No, you are wrong....you have to be wrong...I'm not...you...” Dean protested and waved his hands at Castiel. He then looked away from Cas.

“I know how you see yourself. If anyone was their Daddy's blunt instrument it would have been me. I remember the first time I saw your soul. It shown bright even after it had been damaged in hell.”

“In my whole existence the only thing that changed me was you, Dean. I cared for the whole world because of you.”

“Please Cas,” Dean's voice breaks “please don't, I can't do this again.”

“Yes you can, you're strong and brave and you will survive my passing. I have no doubt. ” Cas thought he was just referring to Cas dying once again.

“I love you.”

As he felt the hand land on his should once more Dean felt his lips tremble and tears pour down his face.

“Cas”

The Empty makes it's entrance. 

Castiel tosses him and is stolen once more from Dean.

Dean lets his tired head fall and waits for his next chance to change things.


	2. What is Love?

**Summary for the Chapter:**

> More of Dean's attempts to stop losing Castiel.

**Notes for the Chapter:**

> Chapter Title reference to 'What is Love?' specifically the Jaymes Young version

~

He found himself coming back to consciousness standing hunched over near the entrance to the room. Dean blinked as he looked over to see Castiel finishing up painting a protective sigil.

The grip on his heart eased.

_'This is going to kill me. This is too much...'_

Dean fell down on his knees palms on the cool concrete floor.

“Dean ” Cas says with concern. He offers him a hand to get up off the ground.

Dean smacks it away in a frustrated motion with causes Cas to furrows his brow.

“I think I'm gonna stay here.” Dean muttered hunched over tears forming. He whispered to himself “I can't watch you die again.”

“Dean we are going to fight this.”

“We're going to lose” Dean replies with a certain tone in his voice. 

“I know one thing that she is afraid of.”

_'There it is'_

Cas's words buzzed in his ears.

He was tired. He couldn't remember the last time that he had felt like this. He somehow felt like he could fall unconscious due to exhaustion. And that he was too wired from all of the fighting of this never-ending nightmare to ever sleep again.

He continued to think up a plan as Castiel spoke.

_'Maybe a rejection would work?'_

“The one thing I wanted is something I know I can't have.”

“Is this a love confession?” Dean interrupts as he raises himself off of the ground.

“Yes.” Cas says with a smile and a crinkle of his blue eyes. “Yes it is.”

_'Showtime.'_

Dean takes a breathe as if this was the first time he had those words said to him from his angel.

“I'm so sorry Man, I think you are just barking up the wrong tree.” Dean says looking at the ground quickly. He has his hands clenched into fists. _Lie._

“Buddy I gotta tell you, I couldn't have expected this from you.” _Not a lie. ___

____

____

“You are still best friend and...” _Not a lie._

He swallowed a lump in his throat as he turned his whole body from Castiel to face the wall that he had been thrown against in many many of the previous loops.

“... brother” _Lie_

He had conned and lied before. Dean had practiced until he was an expert at shoving his feelings and wants inside small boxes.

But these actions were much easier when he believed that Cas did not have the capability for Romantic feelings towards him.

When Cas was beating him to a bloody pulp due to Naomi's brainwashing, he chickened out by saying that he “needed him”.

When Sammy did his younger sibling teasing of the “Destiel” shipping, he deflected instead of broaching the sensitive subject.

When Charlie commented that Cas sounded dreamy. Dean wasn't obvious knew what the she was hinting at. She was gay, she probably could tell that Dean was not as straight as he had attempted to be since he was 17.

“I care about you.” _Truth._

“I did not think you would feel the same way Dean, it's fine with me that you see me as a friend and family.” Cas replies was a pure open smile showed that he was not lying.

“I love you,”

The Empty arrived on schedule

“No no! You can't be happy!” Dean cried in frustration as he approached him and took a hold of his trench coat. “I just turned you down!”

He knew if he himself were to receive a rejection from Cas he would have been devastated. But also that would have required a level of vulnerability that Dean was afraid of.

Cas was always braver than he was.

“Dammit Cas, have some more self respect, you deserve better!” he says releasing his grip from the coat.

“Goodbye Dean.” he says as he applies the bloody hand print in what has become almost comforting at this point.

He still does not care for the shoving.

Somehow he finds more and more hatred in his heart for The Empty each time.

~

Dean momentarily blacked out as his heart began to physically fail him. He found himself coming back to consciousnesses standing hunched over near the entrance to the room. Dean blinked as he looked over to see Castiel finishing up painting a protective sigil on the door with his angelic blood.

Dean could feel the literal death grip on his heart ease.

He took a determined step to the door and gently shoved Cas to the side.

He opens the door and waves the white flag. Billie looks shocked at him with a raised eyebrow.

“What is this Winchester?”

“Billie I surrender but don't take Cas, please.” he holds his hands up. 

“Dean no, stop!” Cas demands as he takes a strong hold of Dean's green jacket. It's not quick enough though.

Last thing Dean sees is a scythe and the shocked face of Castiel.

~

Dean momentarily blacked out as his heart began to physically fail him. He found himself coming back to consciousnesses standing hunched in his usual spot. Dean blinked in aggravation as he looked over to see Castiel finishing up painting a protective sigil on the door with his angelic blood.

Dean could feel the literal death grip on his heart ease.

_'Fuck I thought that was the answer!'_

“Before you even think of summoning the Empty I'm telling you to STOP!” He pointed an accusatory finger the the other man's surprised face.

“The Empty? Cas exclaimed like the idea was brilliant. “That's it! When Jack was dying I made a deal....wait how did you know Dean?”

“It's not important, But I know you need a moment of happiness. And I refuse to give you that!”

“Dean, I...”

“NO! No nononono! Shut up you Sonvabitch!” Dean growls as he covers his ears “I can't hear you!”

“Dean don't behave like a child” Cas reprimands as he gently pries Dean's hands from his ears rather easily.

“I don't want to hear what you have to say Cas!” he yells at him.

“I don't know what has gotten into you but you are being Winchester Stubborn.”

“Yeah I'm being childish and stubborn and stupid!” Dean nodded along to his statements as walks circles around the chair in the middle of the demon circle. 

“While that is true sometimes, you are also caring...the most caring, selfless human begin I will ever know.”

“Cas I'm telling you have to keep your yap shut.” Dean pleads. “I'm begging you Man!”

“Dean I need to be honest with you. Ever since I pulled you out of hell” a tear rolls slowly down Cas's right eye “Knowing you has changed me. Because you cared I cared. I cared about you, I cared about Sam, I cared about Jack, I cared about the whole world because of you”

Dean tries to keep himself together but a sob escapes his body. 

“You changed me Dean”

_'I fucking hate this.'_

“I love you”

“How dare you tell me this as a goodbye you fucking feathered coward!” Dean replies as he angrily wipes the tears from his eyes as Cas applies the mark to his jacket once more.

“Goodbye Dean” 

Shove 

The Empty

~

Dean wordlessly screams himself hoarse when he began the next loop and is only able to numbly nod along to Cas's words.

“I love you”

When it came for the moment for the Empty to make it's arrival Dean shoves Castiel to Dean's usual spot on the ground.

He attempts to block the primordial being's pursuit of Cas.

It easily flows around him and takes Castiel away.

~

He calls Sam

'Hello you have reached the phone of Sam Winchester'

He calls Jack

''Hello I am Jack....Castiel?! do I say Kline or Kline Winchester???'

He throws the phone against the wall. 

“I love you” 

“Goodbye Dean”

Hand print 

Shove

The Empty

~

“I Love you.”

“Goodbye Dean”

Handprint 

Shove 

The Empty 

Again

~

And again

~

AND AGAIN

~

Dean momentarily blacked out as his heart began to physically fail him. He found himself coming back to consciousnesses standing hunched over near the entrance to the room. Dean blinked as he looked over to see Castiel finishing up painting a protective sigil on the door with his angelic blood.

“Did it work?” Cas asks and receives a nod in return.

He was unsure how many times that he had endured the loop at this point. He desperately gripped at his hair. 

“Cas... Cas, shit...shut up and listen to me.” Dean says tired but unflinching as he moves to place his hands on Cas's shoulders in a reverse of the usual actions. “I have an idea!”

“Yes Dean?”

“The...the Empty...

“the empty?” Cas whispers seemly to himself as Dean sees realization bloom on his face. “Dean...that...that's brilliant....I can”

“I told you SHUT UP!” Dean shouted before covering Cas's month with his hand. 

They both stilled for a moment Cas's eyes widen with shock. Dean was pretty shocked at his actions himself.

Feeling Cas's ever present scruff beneath the palm of his hand was jarring. It seemed unnatural and confusing.

“Cas, it only takes demons and angels and non humans right?” he choked out with a nod of Cas's head as a response.

“So what we gotta do is summon it to gank Billie” Dean smiles and removes his hand from Cas's face. “And then we remove your grace to send The Empty packing.”

“I...how do you know about the deal??” Cas asks with a narrowing of his eyes and his signature head tilt of confusion. “Did Jack say something to you?”

Dean lets Cas assume what he will. He makes a mental note to apologize to the kid for letting him take the blame. He'd explain it to everyone when both him and Cas are safe. 

“I am unsure of this plan Dean...” Cas says “Extracting my own grace it would be immensely painful. I'm unsure....”

“Then I'll do it! It's gotta be better than you committing suicide via Hexxus! Come on..” Dean requests as he reaches into Cas's sleeve where he knew he kept his angel blade.

“I know you have to make some emotional speech to be happy. Blah Blah...I'm not a killer...Blah...I'm motivated by love and whatever bullcrap your delusional brain has made up.”

“Dean...how?” Cas's face was the picture of confusion. “It's not bull excrement. You are not a killer you are not how our enemies see you.”

He continues speaking waving the angel blade around impatiently. 

“Yeah yeah...get on with it...” Dean muttered with the uncomfortable shift of his shoulders. He retreats from the feeling by using sarcasm and humor. He imitated Cas's deep voice “You are the most caring man on earth”

“Dean do not mock me.” the angel commands gruffly as he catches Dean's gaze and holds it with intense emotion.  
Over the years he had grown accustomed to gazing into the clear sky blue eyes. They were always so vivid and at first Dean wondered if that was the grace shinning through. When he met other angels he found it was not the case. When he saw his vessel's original owner, Jimmy, his eyes were not as blue either. 

It was just uniquely Cas.

“You feel more acutely than most and it's truly and deeply moving. You have been through more than most and you have not succumbed to apathy it's a testament to the strength of your heart that it keeps caring.” Cas continued.

He already felt uncomfortable with casual compliments. This heartfelt confession was just too much, it really made him feel like he needed to deflect and run.

“Cas...”

“No it's your turn to shut up.” Cas interrupts sternly, Dean nervously licked his lip and stayed silent.

“You told me to speak and I am now doing so. I need to let you know that knowing you has changed me. I care because you care. I care about Sam, Jack, I care about the whole world because of you.” 

Dean bit his lip as he heard the more familiar collective of words. 

“You've changed me.”

“I love you.” Cas says with a small chuckle.

Dean gave a small nod and sad smile in return. He then nervously clears his throat with a cough as the Empty materializes.

Dean remembered what the next sentence would be an he preemptively spoke.

“Don't say goodbye, Cas this has to work.” Dean says with doubt coloring his words.

“Ok here we go.” Dean says moving the angel blade in his hand as he watched The Empty whisk Billie away.

“I just get the grace from your throat right?!” Dean says before he raises the points the tip of the blade to Castiel's neck. 

“Dean it will be right here.” Cas says as he swipes a hand across his neck to show Dean where precisely to cut. 

He gently takes a hold of the back on his head with his free hand. His hands shakes as he carefully slices into Castiel's throat at the instructed point.

A bit of the bluish white radiance trickles out of the laceration.

Dean tries to keep an eye on the rapidly advancing black goo.  
And back to Cas.  
And back to the goo in quick succession

He hears a noise a haunting horrible gurgle. 

His green eyes meet wide blue ones.

Cas clutches at his throat with both hands and Dean drops the blade with a deafening clang

“NO!!! CAS NO!!!!!” Dean shouts while Cas weakly descents to the floor.

He quickly catches Castiel before he hits the ground as his own knees to the concrete.

The grace pours out of Cas's bloody wound and a gush of dark scarlet liquid comes out of Cas's mouth. Dean feels time slow down in the gruesome moment as he watched the man in his arms struggle to breath, to speak, blood filling his lungs.

Dean pulls Cas's head into his lap, now Castiel staring up at the hunter. One hand reaches for Dean's face tenderly. Dean quickly replaces his hand at the hemorrhage. It does little to stop the flow of red.

“NO Cas...Cas I”M SORRY NO! PLEASE CAS!!!!!” Dean feels his voice breaking more than he hears it. The only thing he hears is his own blood rushing loudly in his ears.

Cas's face settles into a resolute sort of peace, it reads to Dean as clearly as if he were speaking _'I don't blame you Dean. You tried everything you could.'_

As the last of the grace flows way his eyes lose that ever present light.

He grief-stricken cries and sobs rack his body as he hugs Castiel's limp and heavy body close. Blood literally covering Dean's hands.

~


	3. Silence

**Notes for the Chapter:**

> Chapter Title is named after Silence- (Originally by Marshello, Khalid) the Illium Remix or the cover by Our Last Night.

~

Please enjoy....while you can.

~

Dean momentarily blacked out as his heart began to physically fail him. He found himself coming back to consciousnesses standing hunched over near the entrance to the room. Dean blinked with determination as he looked over to see Castiel finishing up painting a protective sigil on the door with his angelic blood.

The sight of Cas's blood now turned Dean's stomach. He wipes his palms against his jeans to try and wipe the memory of his hands soaked with it. He could feel the echo of pain on his knees.

He wanted nothing more to rush over to the angel to embrace him and tell him how thankful he was that he was alive. 

But that would not guarantee that he was survive this time loop. Dean was so tired, tired to the bone. But still he forced his body to move the demon circle near the chair and place his hands on the back of the chair for support.

“It worked” Dean prematurely answers Cas's question about the sigil.

_'Maybe I've been doing this wrong....'_

Dean took a shaky breath.

_'Make it so leaving is painful. Then it CAN'T be his happiest moment!'_

“There is something...” Cas begins working out his personal suicide mission.

_'It's his happiest moment because just telling me how he feels, getting that secret out...that weight off his chest is what he thinks is the best he could get.'_

He looks fondly over to Castiel, watching him speak.

_'Just like him to settle for something. I treat him awful...I'_

When Jack was dying, I...I made a deal” Cas returning his eyes to look at him once more. “To save him.”

_'If we ever get out of this I'll do better'_

_'I have this. It's not like the first time... when I was an open mouthed moron. I have his words burned into my mind forever. Just reply this time.'_

_'Tell him'_

The... the price was my life” Cas says his eyes beginning to water with feeling “When I experienced a moment of true happiness The Empty would be summoned and it would take me forever”

“Because the one thing I want is something I know I can't have.”

_'This is your moment! Go on say something! Say something like, yes you can...or I want that too...Something!!!!'“_

“I always wondered” Cas's face turned to look away for the briefest of moments before he quickly found the resolve to turn his gaze fully at Dean. “Ever since I took that burden, that curse, I wondered what it could be. What my true happiness could even look like?”

“But I think I know, I think I know now. Happiness isn't in the having...it's in just being it's in just saying it.”

_'You are my happiness too Cas..... ….. Come on you Dumbass!?!? He's pouring his heart out to you! The bare minimum you can do is say it back!'_

Cas has a brighter expression on his face as he takes a step forward towards Dean.

“I know, I know how you see yourself Dean. You see yourself the same way our enemies see you.

_'Damnit maybe I should quote something! What was that one from that Jane Austen movie that Jack had us watch “If I loved you less I could speak about it more”?....shit ...I can't say something like that...'_

Dean stares Cas unable to sort through everything that he could say in return. 

“You're destructive, you're angry, You're Broken. You're Daddy's blunt instrument.”

_'No Cas I am broken... you know who I am. But you love me anyway'_

“You think that hate and anger that's what drives you, that's who you are.”

_'I don't deserve you Cas.'_

“It's not. And everyone who know so you sees it. Everything you have done the good and the bad you have done for Love.”

_'You know what, fuck this!'_

Dean harshly takes a hold of the lapels of the beige trench coat that Cas always wore.

Castiel's eyes widen momentarily bewildered as Dean shakes him roughly. Dean intensely looks into Cas's blue irises.

“Dean?” 

“Cas” his voice shakes on the single syllable. His heart pounds hard in his chest. 

Dean pulls him close. 

Close enough that Dean can feel the exhale of Cas's breath,

He inhales that breath deeply.

He gazes down at Cas's lips and licks his own.

The silent moment felt like it was filled with the crescendo of music.

Over a decade of longing. 

And crashes his mouth into Cas's. 

Their lips touched, he finally got a life saving gulp of oxygen. 

They had been moving towards this moment since the Barn, sometimes they ran, some other times they crawled but they were always moving towards this moment.

Every time that Dean had thought about this moment paled in comparison. He didn't have the capability to imagine the world shifting into place due to the touching of lips. 

He let go of the coat and wipes the tear that had been lingering on Castiel's cheek since 'you've changed me'. He slides his hands to cradle Cas's face. He was particularly finding the scruff beneath the palms of his hands very grounding. 

He was finding it difficult to form fully coherent thought. But one full sentence shouted joyfully inside his mind. 

_'I'm kissing Cas!'_

He felt Cas's hands grip onto both of his shoulders and pull away. Dean eye's still closed tries to follow the the retreating angel's lips. He is prevented in this action by a hand to his chest. He opens his jade colored eyes.

Cas expression looks so bright and relieved.

_'Please! You can't be this happy to leave me!'_

There was no doubt that THIS was Castiel's happiest moment.

_'I'm a goddamed idiot. Of course this wouldn't break the cycle.'_

His smile was truly the most beautiful thing that Dean had ever seen. 

_'At least I got to finally kiss him.'_

The Empty appears behind Dean and he doesn't even bother to turn to look. He can't bear to look away from Cas's face.

But with the culmination of their feelings for each other he also would have to suffer even more than he thought possible at the loss of Cas.

“NO! No Cas you can't abandon me!” Dean demands and then pleads as he clasps his hands together. “I'm begging here!”

“I...” Cas is choked up as he takes a shaky breath with a smile.

“I love you Dean Winchester.” 

Dean moves to hold Cas tightly. He traps his arms beneath his own. Dean shakes as he fully cries. 

It is not a single man tear falling lonely down his face. All of his tears have partners. There is never a moment of dryness on his face.

“And I love you Cas.”

The Empty surrounds them both.

“NO! No you can't have him!!!!” Dean yells at the primordial ooze. 

“Goodbye, Dean.” He whispers into Dean's ear.

Dean tightens his iron hold.

He grinds his teeth together with the strand of his arms.

It is not enough.

The Empty wraps itself around him to hold him in place as it rips Castiel from Dean's arms.

As it releases Dean he falls to back onto his knees, his head falling down with defeat. He places his own hand on the bloody shoulder mark. 

He is left with only the sounds of his own wailing as he waits for the loop to begin again.


	4. In the End

**Notes for the Chapter:**

> Happy Groundhog day everyone.
> 
> Word of warning everyone homophobic language will be used in this chapter. I will be marking where it begins and ends.

~

Dean momentarily blacked out as his heart began to physically fail him. He found himself coming back to consciousness standing hunched over near the entrance to the room. Dean was unable even able to look at Castiel.

The ghost of Castiel's mouth whispered against his own.

“Did it work?” Cas asks

“Uh, huh” Dean mumbles.

Dean just replies the memory.  
The idea of repeating that particular version of the loop was tempting.

__

_‘But that would not stop Cas from dying’_

“There is one thing that can.”

He nodded numbly along to his disclosure of the trade his life for Jack's.

Castiel continues his speech to a Dean who was not capable of listening.

“Because the one thing I want is something I know I can't have.”

All Dean wants to do in that moment is response with his own words.

He was at a complete loss. He didn't know what else he could do. 

__

'I've tried to tell him this is a loop and THAT was a waste of time, I've tried to throw myself into the Empty, and I let myself get cut through by that scythe. I tried to gently reject him....'

__

_'I tried to...tried to..'_

He couldn't finish that sentence in his mind. All his mind came out was the imagery of Cas's blood.

__

_'And last I tried to tell or I guess show him how I felt.'_

_'And nothing'_

“But I think I know, I think I know now. Happiness isn't in the having...it's in just being it's in just saying it.”

_'The problem is that he is still happy. Either someone dies or he gets taken'_

“What are you talking about Man?” he replies automatically.

__

'So what I have to do is make sure we both survive AND he is unhappy,'

Cas has a brighter expression on his face as he takes a step forward towards Dean.

__

'Look at him.'

“I know, I know how you see yourself Dean. You see yourself the same way our enemies see you.

__

'Ruin his happiness'

“You're destructive, you're angry, You're Broken. You're Daddy's blunt instrument.”

_'Take all of the most hurtful things you can think of and say them!'_

“You think that hate and anger that's what drives you, that's who you are.”

_'I don't want to do this'_

“It's not. And everyone who know so you sees it. Everything you have done the good and the bad you have done for Love.”

__

'Come on, Think of something else!'

“You raise your little brother for love, You fought for this whole world for love. That is who you are.”

Dean can no longer hold his gaze.

__

'anything'

“You're the most caring man on earth. You are the most selfless loving human being I will ever know.”

_'Time is running out!'_

Dean had heard Cas's words more than enough time to memorize everything from the words themselves, to the cadence, to the breaks and breaths.

“You know ever since we met, ever since I pulled you out of hell” a tear rolls slowly down Cas's right eye “Knowing you has changed me. Because you cared I cared. I cared about you, I cared about Sam I cared about Jack I cared about the whole world because of you”  
“You changed me Dean”

__

'I just want you to live...no I NEED you to live!'

“Why does this sound like a goodbye” Dean replies his previous words slower to hopefully stall for more time.

He looks at the slowly approaching figure of Cas until he is once again within arms reach.

_'This is save his life'_

“Because it is”

“I love you”

He closes his eyes and clenches his jaw with force to keep his response silent.

Dean hears The Empty appear.

_'Showtime'_

~  
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~  
~  
~

*BEGINING OF SPEECH*

Dean shoves Castiel away.

“What the Hell Cas?!” Dean says forcing his voice out harshly.

Cas looks hurt but still not 

He repeated the words that when he would imagine Castiel would reply to Dean's confession

“I...I'm not interested in that...that is NOT something I Could EVER want!”

Dean felt as though he was swallowing a golf ball.

Cas had previously told him that he understood when Dean gave him the gentle version of a rejection.

So him nodding along to Dean's words were tragic but not surprising.

_'You deserve the world Cas. You deserve much better than this.'_

Dean remembered when he was thirteen or so maybe fourteen. That was when he first realized that he was attracted to boys as well as girls.

It was 1993 or so. He had never heard of the word bisexual so he was conflict incarnate.

He had just enough youthful bravery to try and make a move on a middle school crush.

His name was Mitchell and he had bonded with Dean over a shared interest in music. 

As they sat in the parking lot behind the gas and sip.

He remember every word that the boy had said to Dean in return.

The ones that burned him.

The ones that made him curse himself for ever being so vulnerable.

_'I was never so happy to move away.'_

“I can't believe I thought we were friends! So as we were hanging out, watching movies, you what? Wanted to shove your tongue down my throat?”

“Anytime we touched....I....you” Dean paused his lies momentarily as he catches his voice waver with the wrong sort of emotion. He clears his throat to reset his voice.

“It make my skin crawl”

He could see Cas looking like he was going to say something. Dean would falter if he hears Cas’svoice so he quickly cut him off.

“...You disgust me.”'

He held his breathe and sees that Billie has been taken by The Empty but it has paused as if it was watching the pair.

__

'That must mean I'm ruining this moment for him. Go more hurtful.'

Cas's face looked similar to the time that he kicked the newly human man out of the bunker years ago, confused and hurt.

Dean pulled more of his deeply painful memories to the surface.

When it came to romance he was not brave enough to try again with another boy until he was 16. He was the son of a hunter that they were working on a case with. They were hanging out alone in the motel room.

This time it reciprocated.

But he was caught by his father.

John Winchester was not known for his being a kind and loving parent.

The violence was not what he remembered for years.

It was the words that cut into him for years.

The ones that made him feel guilt and self loathing when he found himself flustered by male attention.

The ones that silenced him.

“I thought I knew you? But you've been lying to me.” Dean paused to take a shaky breath.

The knives that were in his heart for years Dean took them and stabbed them into Cas's heart.

__

'Please be sad enough that I don't have to say anymore.'

“I'm willing to forget about this. You are too useful to keep around on hunts. But if you EVER try to say something like this you're gone!” he hears the anger and hatred in his voice.

He hates many things.

Mitchell

John

Whatever is causing the horror loop.

Himself

_'But not you Cas.'_

He felt like he was in a prison. Like he was trapped in his body watching a living nightmare happen.

But to cause Cas the type of haunting emotional pain that he himself had suffered for years.

_'Maybe this won't hurt as much since he's an angel and human insults don't mean as much...no he understands what words mean and he understands when they are hurtful and hateful. This isn't 2008 Cas!'_

He almost couldn't continue his parroting of his homophobic father's words. 

But his mind conjures images.

Cas peacefully surrendering himself to The Empty.

Cas being killed by Billie

Cas bleeding out.

Cas being forcefully torn from his arms

It propelled him harshly forward.

“You are such a fucking disappointment. You...” he quietly said more to himself as he could not find another way to save his angel.

He whimpered out one final word, a slur, before a lurch of nausea overwhelmed him as forced himself from puking.

“Fag”

~  
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~  
~  
~  
~  
~  
~  
~

*END OF SPEECH*

He turns to stare at the wall, he could not bear to look at Castiel.

“I'm sorry Dean.” Castiel's deep voice sounded so hurt that Dean immediately wanted to turn around and take back the words. Instead he bit the inside of his cheek until he tasted copper.

Out of the corner of his eye he spots The Empty float in front of Cas.

Dean closed his eyes and holds his breathe as he waits for the time loop to start again.

The Empty.

It speaks in a inhuman voice.

**“I wanted you to suffer. This is more painful than anything I could ever do to you.”**

He felt the death grip on his heart more painful than any other time. He opened his eyes expecting to be in his usual spot near the entrance.

****

“You get to live with this, You're welcome.”

He turned his head in shock to see the Shadow get smaller and smaller until it was completely gone. and Castiel's defeated form looking with dull eyes at the floor. 

He quickly returned his eyes to look at the wall.

“We need to go find Sam and Jack.” Cas whispers with a heart wrenching tone moved out of the room. “I...I will meet you at the car.”

Dean fell to the ground catching himself with his hands and he rid his stomach of it's contents.  
He wiped the puke from the corners of his mouth, took another moment and still nothing.

He stands and hits the wall again and again, his body does not allow the relief from tears.

He took a painful punishing grip of his own left shoulder. Where the absence of Cas's hand print solidified the realization that this was the finally the end of the loop.

_'I'm so sorry Cas.'_


End file.
